Kirk as the prototype Guinan and the person who's responsible for all those children under Picard's feet all the time: I love it!

Actually I always thought the point of a barista AU was to point out that the true meaning of life has nothing to do with having squillions and squillions of dollars (or insert your local currency here), and that true happiness can be found anywhere you have friends and caffeine in the same place. But this AU of yours handily does both! Awesome.